4-trimethylammonium-acetophenone iodide | 27853-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-trimethylammonium-acetophenone iodide
• 英文别名: (4-acetylphenyl)trimethylammonium iodide；(4-acetylphenyl)-trimethylazanium;iodide
• CAS: 27853-26-5
• 化学式: C₁₁H₁₆NO*I
• 分子量: 305.159
• InChiKey: XLZNQUVLGHPQFD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.91
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-trimethylammonium-acetophenone iodide 、 偏二甲肼 以 溶剂黄146 为溶剂， 生成 {4-[1-(Dimethyl-hydrazono)-ethyl]-phenyl}-trimethyl-ammonium; iodide
  参考文献：
  名称：

  Monoquaternary neuromuscular blocking agents based on 1-tetralone and 1-indanone

  摘要：

  The preparation of three isomeric 1-tetralone hydrozones 4 and three isomeric 1-indanone hydrozones 5 possessing a single quaternary ammonium center is described. Several of the compounds possessed significant neuromuscular blocking activity, and two approached suxamethonium in potency. 1H NMR evidence obtained from a study of the N,N-dimethylhydrozones indicated that the hydrazones adopted an E configuration in solution.

  DOI：

  10.1021/jm00226a004
• 作为产物：
  描述：

  二甲氨基苯乙酮 、 碘甲烷 以 乙醇 为溶剂， 生成 4-trimethylammonium-acetophenone iodide
  参考文献：
  名称：

  Nitrogen and deuterium kinetic isotope effects on the Menshutkin reaction

  摘要：

  Nitrogen and deuterium kinetic isotope effects were measured in the Menshutkin reaction between methyl iodide and a series of para-substituted N,N-dimethylanilines in ethanol, The nitrogen kinetic isotope effect increases for the more electron-donating substituents [0.9989, 1.0032, and 1.0036 for 4-C(O)Me, H and 4-Me, respectively], in agreement with the Hammond postulate, The secondary deuterium isotope effect, however, exhibits the reverse trend (1.045, 0.989, 0.975 per deuterium, for the respective substituents). This discrepancy is rationalized in terms of solvent molecule participation in the transition state.

  DOI：

  10.1002/(sici)1099-1395(199601)9:1<35::aid-poc753>3.0.co;2-y

文献信息

• Synthesis of Arylstannanes from Arylamines
  作者：Alicia B. Chopa、María T. Lockhart、Gustavo Silbestri

  DOI：10.1021/om000859p

  日期：2001.7.1

  Arylamines have been converted into aryltrimethylammonium salts, which on reaction with sodium trimethylstannide (1) in liquid ammonia afford aryltrimethylstannanes by the SRN1 mechanism. With (4-methoxyphenyl)- (2), (1-naphthyl)- (4), phenyl- (6), (4-acetylphenyl)- (8), and (4-cyanophenyl)trimethylammonium salts (10) the substitution products are obtained in good to excellent yields (45−100%). Also

  芳胺已被转化为芳基三甲基铵盐，其与三甲基锡钠（1）在液氨中反应，通过S RN 1机理得到芳基三甲基锡烷。用（4-甲氧基苯基）-（2），（1-萘基）-（4），苯基-（6），（4-乙酰基苯基）-（8）和（4-氰基苯基）三甲基铵盐（10）进行取代产品的收率好至极好（45-100％）。同样，（2-吡啶基）三甲基碘化铵（12）与1的光刺激反应导致取代产物13（50％）。与（4-氯苯基）三甲基碘化铵（14）以76％的产率获得分散产物19。另一方面，在（4-溴苯基）三甲基碘化铵（15）与1的反应中获得的结果清楚地表明在黑暗中快速的HME反应。ET工艺（S RN 1）虽然在辐射下效率低下，但竞争激烈。
• McClelland, Robert A.; Engell, Karen M.; Larsen, Truels S., Journal of the Chemical Society. Perkin transactions II, 1994, # 10, p. 2199 - 2206
  作者：McClelland, Robert A.、Engell, Karen M.、Larsen, Truels S.、Soerensen, Poul E.

  DOI：——

  日期：——
• BIGGS D. F.; CASY A. F.; CHU I.; COUTTS R. T., J. MED. CHEM. <JMCM-AR>, 1976, 19, NO 4, 472-475
  作者：BIGGS D. F.、 CASY A. F.、 CHU I.、 COUTTS R. T.

  DOI：——

  日期：——
• Monoquaternary neuromuscular blocking agents based on 1-tetralone and 1-indanone
  作者：D. F. Biggs、A. F. Casy、Ih Chu、R. T. Coutts

  DOI：10.1021/jm00226a004

  日期：1976.4

  The preparation of three isomeric 1-tetralone hydrozones 4 and three isomeric 1-indanone hydrozones 5 possessing a single quaternary ammonium center is described. Several of the compounds possessed significant neuromuscular blocking activity, and two approached suxamethonium in potency. 1H NMR evidence obtained from a study of the N,N-dimethylhydrozones indicated that the hydrazones adopted an E configuration in solution.
• Nitrogen and deuterium kinetic isotope effects on the Menshutkin reaction
  作者：A. Szylhabel-Godala、S. Madhavan、J. Rudzi?ski、M. H. O'Leary、P. Paneth

  DOI：10.1002/(sici)1099-1395(199601)9:1<35::aid-poc753>3.0.co;2-y

  日期：1996.1

  Nitrogen and deuterium kinetic isotope effects were measured in the Menshutkin reaction between methyl iodide and a series of para-substituted N,N-dimethylanilines in ethanol, The nitrogen kinetic isotope effect increases for the more electron-donating substituents [0.9989, 1.0032, and 1.0036 for 4-C(O)Me, H and 4-Me, respectively], in agreement with the Hammond postulate, The secondary deuterium isotope effect, however, exhibits the reverse trend (1.045, 0.989, 0.975 per deuterium, for the respective substituents). This discrepancy is rationalized in terms of solvent molecule participation in the transition state.